Sterol extraction with polar solvent to give low sterol, high triglyceride, microbial oil

ABSTRACT

The present invention relates to a process of treating an oil, the process comprising contacting the oil with a polar solvent to extract at least one compound that is soluble in the solvent, and then separating the solvent containing the compound from the so treated oil. The oil is microbially derived, and extracted either from a fermentation broth or a filtrate thereof using hexane. The compound to be extracted is usually a sterol or a diglyceride. The solvent is ethanol having up to 5% water. The oil can contain a polyunsaturated fatty acid such as C18, C20 or C22 ω-3 or ω-6 fatty acid, such as arachidonic acid.

This application is a 371 of PCT/EP97/02510 filed May 5, 1997.

FIELD OF THE INVENTION

The present invention relates to purified (such as by extraction)polyunsaturated fatty acid (PUFA)-containing (microbial) oils,especially oils with a triglyceride content of at least 97% and/or asterol content of either less than 1.5% or greater than 10%.

BACKGROUND OF THE INVENTION

There is a growing tendency to include lipid products containingpolyunsaturated fatty acids derived from various fermentation processesin foodstuffs. This is of importance in the recently establisheddesirability to incorporate certain polyunsaturated fatty acids in aninfant formula.

Various processes have been described for the fermentative production oflipids or oils containing polyunsaturated fatty acids. Examples areEP-A-155,420 for the production of γ-linolenic acid (GLA)-containinglipid from Mortierella, EP-A-223,960, EP-A-276,541 and WO-A-92/13086 forthe production of arachidonic acid (ARA)-containing oil from Mortierellaand/or Pythium, WO-A-91/07498 and WO-A-91/11918 for the production ofdocosahexaenoic acid (DHA)-containing oil from Crypthecodinium cohnii orThraustochytrium, and WO-A-91/14427 for the production ofeicosapentaenoic acid (EPA)-containing oil from Nitzschia. Typically,the microbial species producing the lipid containing the desiredpolyunsaturated fatty acid(s) is cultured in a suitable medium and thebiomass is harvested before the desired lipid obtained.

To obtain a lipid concentrate which has a relatively high triglyceridecontent typically a nonpolar solvent for the lipid (e.g. hexane) orsupercritical CO₂ is used in the extraction process. For example,EP-A-246,324 describes a fractional extraction process for the isolationof lipids from Mortierella, to obtain different extracts which areenriched in either polar or nonpolar (neutral) lipids. The neutral lipidextract still has, however, a relatively low triglyceride content(89.3%) and a high sterol content (9.4%). U.S. Pat. No. 4,857,329describes an extraction process comprising the use of supercritical CO₂to selectively elute neutral lipids from Mortierella biomass. However,the triglyceride content of the lipid extract does not exceed 86%.

Yamada et al, Industrial applications of single cell oils, Eds. Kyle andRatledge, 118-138 (1992) describe an arachidonic acid-containing oilextracted from Mortierella alpina biomass using hexane. The purified oilhas a triglyceride content of 90%.

Thus, until now it has not been possible to obtain a microbialtriglyceride oil with a high triglyceride content, i.e. 95% or higher,using previous fermentation and extraction technology. It has also notbeen possible to prepare oils having a particularly low (e.g. less than1.5%) or high (e.g. at least 10%) sterol content.

DESCRIPTION OF THE INVENTION

The present invention generally relates to a process for preparing a(microbial) oil with a high triglyceride content and a low content of"unsaponifiables", where an oil extracted, obtained or derived from amicrobial biomass is treated with a polar solvent.

The present invention can thus provide a microbial (or microbiallyderived) oil having a high triglyceride content, such as ≧95%. Howeverthe oil may have a triglyceride content of at least 97%, preferably≧98%, and optimally ≧99%. The (microbial) oil may alternatively or inaddition have a low (e.g. ≦1.5%) or high (e.g. ≧10%) sterol content.Preferably the sterol content is ≦1%, such as ≦0.6%, optimally ≦0.3%.

The oil of the invention can be used in various compositions such aspharmaceutical (or therapeutic), cosmetic, feedstuff or foodcompositions (for human or animal consumption), especially in an infantformula or nutritional supplement.

A first aspect of the present invention therefore relates to a processof treating a microbially derived oil (an oil derived from amicroorganism), the process comprising contacting the oil with a polarsolvent to extract at least one compound that is soluble in the solvent,and separating at least some of the solvent containing the compound fromthe (so treated) oil.

The microbially derived oil can be extracted, obtained, or produced byone or more microorganism(s). Often this will be the same species ofmicroorganism, but a mixture of two or more different microorganisms areenvisaged by the invention. The process of the invention may thereforebe subsequent to the production of the oil itself. The oil may be onethat is produced by, or exists inside (e.g. intracellularly) themicroorganism(s). Alternatively, it may be obtained from a (usuallyaqueous) composition obtained or resulting from fermentation (of themicroorganisms). This (aqueous) composition may contain themicroorganisms themselves: in that case, it is usually a fermentationbroth. The microorganisms (or biomass as referred to in the art) can beremoved (after fermentation) by a number of methods, for examplefiltration, centrifugation or decantation. The oil can be extracted orobtained from this biomass.

It is usual that the microbial oil will have been obtained byextraction. This preferably will have involved extraction using anon-polar, or preferably a water-immiscible, solvent, or at least asolvent that is capable of extracting oily components. Such a solventmay be a C₆₋₁₀ alkane, for example hexane, or (supercritical) carbondioxide.

Different microorganisms will produce different oils. These can differin the amount of polyunsaturated fatty acids (PUFAs) as well as in othercomponents, and indeed the PUFAs may be in different forms, for examplediglycerides, triglycerides and/or phosolipids. As such, evenmicrobially derived oils can differ significantly from oils containingone or more of these PUFAs that have been obtained from other (e.g.animal or fish or vegetable) sources.

The microorganisms contemplated can vary widely, although preferablythey will be able to produce one or more PUFAs, for example onfermentation. Microorganisms can be bacteria, algae, fungi or yeasts.Suitable fermentation processes, microorganisms and PUFA-containing oilsare described in co-pending International application no. PCT/EP97/01448(filed on Mar. 21, 1997 in the name of Gist-brocades B.V.), the contentof which is incorporated herein by reference.

Preferred algae are of the genus Crypthecodinium, Porphyridium orNitzschia. Preferred fungi are of the genus Thraustochytrium,Mortierella, Pythium, Mucorales or Entomophthora, in particular of thespecies Mortierella alpina.

The compound to be extracted can either be a desired compound, where thecompound is to be purified or even isolated, or it may be an impuritythat one wishes to remove from the oil. Generally speaking, the compoundwill fall into the latter category. Thus, the compound may be an"unsaponifiable", in other words one that is not solubilized (in water)after treatment with an alkali (e.g. NaOH) and so does not form a salt(thus it may not be capable of saponification). other compounds includesterols, which can be alicyclic alcohols having a four conjugated ringbackbone, three aromatic C₆ rings and one cyclopentane ring (e.g.desmosterol, cholesterol) aliphatic and terpenic alcohols, tocopherol),waxes and antifoaming agents, such as polypropylene glycol, which may bepresent in the fermentation medium.

A second aspect of the present invention relates to a process oftreating an oil comprising at least one sterol, the process comprisingcontacting the oil with a polar solvent to extract as least one sterolthat is soluble in the solvent, and separating at least some of thesolvent containing the sterol from the oil.

Preferred sterols include desmosterol, such as 5-desmosterol. If morethan one sterol is present, then suitably 70 to 90%, e.g. 80 to 85%, ofthe sterols is desmosterol (e.g. for oil produced by Mortierella.

The oil will preferably contain at least one PUFA. This PUFA willusually have been produced by the microbe or microorganism.

A third aspect of the invention relates to a process for preparing anoil comprising at least one polyunsaturated fatty acid (PUFA), theprocess comprising treating an oil comprising at least one PUFA and atleast one sterol with a polarsolvent to extract at least some of thePUFA and at least some of the sterol (into the solvent), both the PUFAand the sterol being at least partially soluble in the solvent,separating the solvent (phase) from the oil (phase), and evaporating orotherwise removing some of the solvent to give a (residual) oil having asterol content of at least 10%.

This sterol content may be even higher, such as at least 11%, forexample at least 14%.

PUFAs contemplated by the invention are C20 and C22 ω-3 and C18, C20 andC22 ω-6 polyunsaturated fatty acids. In particular they can includeγ-linolenic acid (GLA), dihomo-γ-linolenic acid (DLA), arachidonic acid(ARA), eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). DHAis produced by algae or fungi, such as a dinoflagellate algae, forexample of the genus Crypthecodinium, or a fungus, for example of thegenus Thraustochytrium. GLA, DLA or ARA can be produced by fungi, suchas of the genus Mortierella, Pythium or Entomophthora. EPA can beproduced by an algae, such as of the genus Porphyridium or Nitzschia.Typically the oil will dominantly or only contain one PUFA, althoughoils can contain one or more PUFAs, for example in a lesser amount.

In the processes of the invention after the solvent has been added tothe oil, the two phases (oil and solvent) will usually separate. Thiscan easily then allow removal of one phase from the other.

It will be realised that in the second aspect of the invention one isextracting a sterol from the oil. That can then give an oil with a lowsterol content, for example no more than 1.5%. The third aspect relatesto the processing of that solvent, in which some of the oil and sterolhas dissolved. That solvent will thus be relatively sterol rich: aftersome of the solvent has been removed, one is left with a "residual" oilwhich can have a sterol content of at least 10%.

A fourth aspect of the invention therefore relates to an oil treated orprepared by a process according to any of the first to third aspects.

A fifth aspect relates to an oil, comprising at least onepolyunsaturated fatty acid that has been produced by a microorganism,having a sterol content of no more than 1.5%. The (total) sterol contentmay in fact be no more than 1%, for example less than 0.6%. By using theprocesses of the invention, a sterol content of no more than 0.3% can beachieved.

A sixth aspect relates to an oil, comprising at least onepolyunsaturated fatty acid produced by a microorganism, having a sterolcontent of at least 10%.

It will be realised that the oil of the fifth aspect can be prepared byusing the process of this second aspect, while the oil of the sixthaspect can be prepared using the process of the third aspect.

The different oils of the invention can be prepared, for example, byusing different solvents, at different temperatures, as will bedescribed later.

The present invention therefore provides a process for preparing an(e.g. microbial) oil, where the oil is treated with one or more polarsolvents. These solvent(s) can therefore remove one or more compoundsthat are soluble in the solvent. This may result in concentrating orenriching of the oil. Therefore, if the oil contains triglycerides, onecan concentrate or increase the triglyceride content of the oil. Thismay be to at least 97%, for example at least 98%, and ultimately atleast 99%.

Simultaneously with increasing the triglyceride content, the solventtreatment can advantageously result in the removal of one or moreimpurities from the oil. In particular, this treatment can result in thelowering of the amount of "unsaponifiables". These unsaponifiables thatcan be removed by the solvent treatment can include the sterols,aliphatic and terpenic alcohols, waxes and antifoaming agents describedearlier. Usually, the treatment of the solvent will not alter the PUFAprofile or the oil so treated.

The polar solvent preferably comprises a C₁₋₆ alkanol, for exampleethanol. The solvent, however, may be an aqueous one. Preferred solventstherefore comprise an alcohol (e.g. ethanol) and water. However, thesolvent may comprise other liquids, and these can be acetone and/orisopropanol.

If the solvent comprises ethanol, this may have a water content of from0 to 20%, such as from 1 to 7%, and optionally from 2 to 4%. If thesolvent comprises methanol, acetone and/or isopropanol (IPA), then thewater content is preferably 0 to 2%, 5 to 50% and 5 to 15%,respectively. The solvent may therefore comprise a mixture of two ormore liquids. It has been found that ethanol containing a small amountof water (e.g. 97% ethanol, 3% water) can significantly improve theyield of triglyceride after solvent treatment. This is becausetriglycerides are relatively insoluble in this particular solvent.Having the solvent at a temperature of from 15 to 30° C., e.g. 20 to 25°C., also reduces the amount of triglycerides that dissolved in thesolvent.

By using different solvents one can vary the amount of sterol (or indeedPUFA) that is extracted. As has been discussed above, a mix of ethanoland water can provide a high yield of triglycerides since although thissolvent will dissolve sterols, triglycerides are nevertheless relativelyinsoluble in it.

The PUFA will generally exist in several forms, such as triglyceridesand diglycerides. These compounds are effectively a glycerol moleculewith one or more (although usually only one) of the PUFAs attached tothis backbone. Preferably the triglyceride form will be dominant. In theoil of the fifth aspect (e.g. from the process of the second aspect),the amount of diglycerides present is preferably no more than 2.2%, andpreferably less than 1%. The solvent used here is preferably at atemperature of from 10 to 40° C., e.g. 20 to 30° C.

In the oil of the sixth aspect, the relative ratios of triglycerides anddiglycerides can change. In the preparation of this oil, a solvent ischosen to extract not only the sterol, but also some of thetriglycerides and diglycerides present in the original oil. Thetriglyceride content may therefore vary from 60 to 90%. The diglyceridecontent may vary from 5 to 25, such as from 12 to 22%. It was found thatethanol with 3% water could be a solvent for the diglycerides (andtriglycerides) and so this solvent is suitable for use in the process ofthe third aspect, for example to produce an oil according to the sixthaspect. Here the solvent is preferably employed at a temperature of from50 to 70° C., e.g. 55 to 65° C.

The amount of compound to be extracted, or the triglyceride content, canbe adjusted by varying several process parameters. For example, one canadjust the ratio of solvent to oil, the temperature during extractionand/or by repeating the extraction process. If more than one extractionis to be performed, a counter-current extraction process is preferred,which can minimise triglyceride losses.

Usually the oil will be a crude oil obtained after extraction from a(e.g. dried) microbial biomass with a suitable solvent, followed byevaporation of that (water immiscible) solvent. The oil may be subjectedto one or more refining steps prior to the process of the invention.

The oil of the invention, or one which results from a process of thefirst, second or third aspect, can be used for various purposes withoutfurther processing, or can be additionally subjected to one or morerefining steps. The oil can be used as an additive or a supplement, forexample in food compositions, such as an infant formula. It may howeveralso be used in cosmetic or pharmaceutical compositions. The inventionin a further aspect therefore relates to a composition, such as a foodstuff, feed or pharmaceutical composition or a cosmetic composition,which comprises, or to which has been added, an oil of the invention.Preferred compositions are foods, such as infant formula or anutritional supplement.

The oil of the invention can therefore have a low sterol and/or lowdiglyceride content. It may also have a high triglyceride content. Thismakes the oil particularly suitable for nutritional purposes, and can beused as a nutritional supplement. The oil may be supplied as an oil, orit may be encapsulated, for example, in a gelatin capsule. The oil canthus be incorporated in foods, feeds or foodstuffs, suitable for humanor animal consumption. Suitable examples are health drinks and bread.Particularly contemplated is the use in infant formula, or in cosmetics.

Preferred features and characteristics of one aspect of the inventionare equally applicable to another aspect mutatis mutandis.

The invention will now be described, by way of example, with referenceto the following Examples which are provided merely for means ofillustration, and are not to be construed as being limiting on theinvention.

COMPARATIVE EXAMPLE 1

Recovery of crude ARA oil from M. alpina biomass

500 l of broth obtained after Mortierella alpina fermentation wasfiltered in a membrane filter press (cloth type: propex 46K2). The brothwas filtered with a pressure difference of 0.2 bar. Within 21 minutes500 l broth was filtered over a total filter area of 6.3 m² whichresulted in an average flow of about 230 l/m² h. The filter cake waswashed in 30 minutes with 10 cake volumes of tap water at an averageflow rate of 320 l/m² h.

The cake was squeezed at 5.5 bar for 30 minutes which resulted in a drymatter content of the recovered biomass of about 45%.

Extrusion was performed on the resulting biomass cake using a singlescrew extruder with a profiled barrel and a universal screw. Thedieplate used for extrusion had holes of diameter 2 mm.

Drying of the extrudate was performed in a fluidized bed dryer with air(8000 Nm³ /m² h). The setpoint of the bed temperature was 80° C. Thediameter of the dried extruded biomass was 2 mm and its dry mattercontent after drying was about 96%.

A crude arachidonic acid-containing oil (ARA oil) was then extractedfrom the extrudate using hexane as a solvent.

EXAMPLES 2 AND 3

Treatment of microbial ARA oil with 100% ethanol

5 ml of crude ARA oil was extracted from the extrudate of Example 1 witha volume of 100w ethanol for 1 minute by hand-shaking. Subsequently, thebottom and toplayers were separated by centrifugation for 5 minutes at5000 rpm. The samples were analyzed by means of (600 Mhz) NMR (for tri-and di-glycerides, sterols (only desmosterol content measured) andantifoaming agent).

Extraction of crude ARA oil with 9 volumes of 100t ethanol at twodifferent temperatures resulted in an oil with a decreased level ofsterol and diglyceride (DG) and in an increased level of triglyceride(TG, see Table 1). The yield of TG is the percentage of triglycerideremaining in the oil after solvent extraction. Also antifoaming agentwas removed and found in the ethanol after extraction. However, theyield of triglycerides was low due to the fact that some of the TGdissolved (and was thus removed in) the ethanol.

                  TABLE 1                                                         ______________________________________                                        Extraction of crude ARA oil with 100% ethanol                                   (data for treated oil)                                                        Ex     solvent   temp. % TG  % DG  % sterol                                                                            yield TG                           ______________________________________                                        --   Control   --      96.2  2.2   1.6   100                                    2 EtOH 100% ambient 98.2 0.7 1.1 73.8                                         3 EtOH 100% 60° C. 98.5 0.7 0.8 43.2                                 ______________________________________                                         Key:                                                                          TG: triglycerides                                                             DG: diglycerides                                                              Sterol: as desmosterol                                                   

EXAMPLES 4 TO 9

Treatment of microbial ARA oil with 97% ethanol

Examples 2 and 3 were repeated except using 97% ethanol at varyingvolumes relative to the oil.

Extraction of crude ARA oil with 1, 3 and 9 volumes of 97% ethanolresulted in an oil with a decreased level of sterol and diglyceride andin an increased level of triglyceride (see Table 2).

The yield of triglycerides was above 92% due to the fact that not muchoil dissolves in 97% ethanol. At ambient temperature (about 20° C.), ahigher yield of triglycerides and a better removal of diglycerides andsterols was observed. Remarkably no ethanol was found in the treatedoil.

                  TABLE 2                                                         ______________________________________                                        Extraction of crude ARA oil with 97% ethanol                                    (data for treated oil)                                                                              vol              %                                      Ex solvent temp. EtOH % TG % DG sterol yield TG                             ______________________________________                                        --  Control   --      0    96.2  2.2   1.6  100                                 4 EtOH 97% ambient 1 96.7 1.8 1.4 92.9                                        5 EtOH 97% ambient 3 97.8 1.1 1.1 95.0                                        6 EtOH 97% ambient 9 98.9 0.4 0.7 96.2                                        7 EtOH 97% 60° C. 1 96.4 2.0 1.6 99.7*                                 8 EtOH 97% 60° C. 3 97.7 1.1 1.2 92.4                                  9 EtOH 97% 60° C. 9 98.3 0.6 1.1 93.7                                ______________________________________                                         Key:                                                                          TG: triglycerides                                                             DG: diglycerides                                                              Sterol: as desmosterol                                                        *Due to the increase of the lower (oil) phase because the ethanol partly      dissolved into the oil and so phase separation was more difficult.       

The ethanol phase was also analyzed after extraction and a significantincrease in sterols was observed. Also the antifoam agent (polypropyleneglycol) was extracted and found in the ethanol phase (see Table 3).

                  TABLE 3                                                         ______________________________________                                        Extraction of crude ARA oil with 97% ethanol                                    (data for ethanol phase)                                                                            vol              %      %                               Ex solvent temp. EtOH % TG % DG antifoam sterol                             ______________________________________                                        4   EtOH 97%  ambient 1    60.9  20.8  4.1    14.2                              5 EtOH 97% ambient 3 73.1 15.3 1.3 10.2                                       6 EtOH 97% ambient 9 83.0 10.0 0.7 6.3                                        7 EtOH 97% 60° C. 1 66.1 18.3 3.7 11.9                                 8 EtOH 97% 60° C. 3 78.6 12.5 1.1 7.8                                  9 EtOH 97% 60° C. 9 87.9  7.1 0.4 4.5                                ______________________________________                                         Key:                                                                          TG: triglycerides                                                             DG: diglycerides                                                              Sterol: as desmosterol                                                   

What is claimed is:
 1. A process of treating an oil derived from amicroorganism, the process comprising:(a) contacting the oil with apolar solvent to extract at least one sterol that is soluble in thesolvent; and (b) separating at least some of the solvent containing thesterol from the oil, wherein the oil has a sterol content of less than1.5%.
 2. A process according to claim 1 when the oil is obtained orextracted from a composition resulting from a fermentation.
 3. A processaccording to claim 2 when the composition is a fermentation broth.
 4. Aprocess according to claim 2 wherein the oil is derived, obtained orextracted from microorganisms present in the composition.
 5. A processaccording to claim 4 wherein the microorganisms are first removed fromthe composition.
 6. A process according to claim 5 wherein themicroorganisms are first removed by filtering the composition.
 7. Aprocess according to claim 5 wherein the microorganisms are dried beforethe oil is obtained.
 8. A process according to claim 2 wherein the oilhas been extracted using a solvent for triglycerides.
 9. A processaccording to claim 8 when the solvent is hexane, supercritical carbondioxide or isopropanol.
 10. A process according to claim 1 wherein theoil is produced by, or the microorganisms is, a bacterium, fungus, yeastor alga.
 11. A process according to claim 10 when the microorganism isof the genus Crypthecodinium, Mucorales, Thraustochytrium, Mortierella,Pythium, Entomophthora, Porphyridium or Nitzschia.
 12. A processaccording to claim 1 wherein the oil is derived from Mortierella alpina.13. A process according to claim 1 wherein the sterol is produced by, oris present intracellularly inside, the microorganism.
 14. A processaccording to claim 1 wherein the sterol is desmosterol.
 15. A processaccording to claim 1 when the oil comprises at least one polyunsaturatedfatty acid (PUFA).
 16. A process according to claim 15 herein the PUFAis a C18, C20 or C22 ω-3 or ω-6 polyunsaturated fatty acid.
 17. Aprocess according to claim 16 wherein the PUFA is GLA, DLA, ARA, EPA orDHA.
 18. A process for preparing an oil comprising at least onepolyunsaturated fatty acid (PUFA), the process comprising:(a) treatingan oil derived from a microorganism and comprising at least one PUFA andat least one sterol with a polar solvent to extract at least some of thePUFA and at least some of the sterol, both the PUFA and sterol being atleast partially soluble in the solvent; and (b) separating the solventfrom the oil, and evaporating or otherwise removing some of the solvent,to give a (residual) oil having a sterol content of at least 10%.
 19. Aprocess according to claim 18 when the sterol is desmosterol.
 20. Aprocess according to claim 18 wherein the PUFA is a C18, C20 or C22 ω-3or ω-6 polyunsaturated fatty acid.
 21. A process according to claim 20when the PUFA is GLA, DLA, ARA, EPA or DHA.
 22. A process according toclaim 1 wherein the solvent comprises a C₁₋₆ alkanol or acetone.
 23. Aprocess according to claim 22 wherein the solvent is ethanol orisopropanol.
 24. A process according to claim 1 wherein the solventcomprises ethanol and from 1% to 5% water.
 25. A process according toclaim 1 wherein the amount of solvent used in the extraction is from 1to 9 times the volume of the oil to be treated.
 26. A process accordingto claim 18 wherein the solvent comprises a C₁₋₆ alkanol or acetone. 27.A process according to claim 26 wherein the solvent is ethanol orisopropanol.
 28. A process according to claim 18 wherein the solventcomprises ethanol and from 1% to 5% water.
 29. A process according toclaim 18 wherein the amount of solvent used in the extraction is from 1to 9 times the volume of the oil to be treated.
 30. An oil treated orprepared by a process according to claim
 1. 31. An oil, comprising atleast one polyunsaturated fatty acid (PUFA) that has been produced by amicroorganism, having a sterol content of no more than 1.5%.
 32. An oilaccording to claim 31 having a sterol content of no more than 1%.
 33. Anoil treated or prepared by a process according to claim
 18. 34. An oilcomprising at least one polyunsaturated fatty acid (PUFA) produced by amicroorganism, having a sterol content of at least 10%.
 35. In apharmaceutical, cosmetic, feed or foodstuff composition for consumptionby humans or animals having active ingredients wherein the improvementcomprises as an active ingredient the oil according to claim
 30. 36. Acomposition comprising, or to which has been added, an oil according toclaim
 30. 37. A composition according to claim 36 which is a foodstuff,feed, cosmetic or pharmaceutical composition or a nutritional supplementfor consumption by humans or animals.
 38. A composition according toclaim 37 which is an infant formula.
 39. In a pharmaceutical, cosmetic,feed or foodstuff composition for consumption by humans or animalshaving active ingredients wherein the improvement comprises as an activeingredient the oil according to claim
 33. 40. A composition comprising,or to which has been added, an oil according to claim
 33. 41. Acomposition according to claim 40 which is a foodstuff, feed, cosmeticor pharmaceutical composition or a nutritional supplement forconsumption by humans or animals.
 42. A composition according to claim41 which is an infant formula.